1048641-05-9Relevant academic research and scientific papers
Photo-promoted Skeletal Rearrangement of Phosphine–Borane Frustrated Lewis Pairs Involving Cleavage of Unstrained C?C σ-Bonds
Ito, Tatsuyoshi,Iwasawa, Nobuharu,Takaya, Jun
, p. 11913 - 11917 (2020)
An unprecedented photo-promoted skeletal rearrangement reaction of phosphine–borane frustrated Lewis pairs, o-(borylaryl)phosphines, involving cleavage of an unstrained sp2C–sp3C σ-bond is reported. The reaction realizes an efficient
Ortho-(Dimesitylboryl)phenylphosphines: Positive boryl effect in the palladium-catalyzed suzuki-miyaura coupling of 2-chloropyridines
Malacea, Raluca,Chahdoura, Faouzi,Devillard, Marc,Saffon, Nathalie,Gomez, Montserrat,Bourissou, Didier
, p. 2274 - 2284 (2013/10/01)
Catalytic systems combining ortho-(dimesitylboryl) phenylphosphines and palladium precursors have been evaluated in the Suzuki-Miyaura couplings of chloro-N-heterocycles, in particular 2-chloro pyridines, with arylboronic acids. The Lewis basic character of the substrates does not interfere with the Lewis acidic site of the ligands, even for a substrate featuring free NH2 groups. The influence of several reaction parameters has been studied and the ortho-dimesitylboryl moiety was actually found to substantially enhance the catalytic performance. The role of this group has been examined using preformed phosphine-borane/Pd complexes and the formation of an original phosphine/h4-boratabutadiene complex has been identified as a possible deactivation pathway. Regioselective coupling of 2,6-dichloro-3-nitropyridine with phosphine-borane/Pd catalysts has also been explored, and sequential double cross-couplings were found to give a direct and efficient access to unsymmetrical 2,6-diarylpyridines.
Fluoride ion chelation by a bidentate phosphonium/borane lewis acid
Hudnall, Todd W.,Kim, Young-Min,Bebbington, Magnus W. P.,Bourissou, Didier,Gabbai, Francois P.
supporting information; experimental part, p. 10890 - 10891 (2009/02/05)
The phosphonium borane [1-Mes2B-2-MePh2P-(C6H4)]+ ([2]+) has been synthesized as an iodide salt by alkylation of 1-Mes2B-2-Ph2P-(C6H4) with MeI. This novel cationic borane complexes fluoride to afford the corresponding zwitterionic fluoroborate complex 1-FMes2B-2-MePh2P-(C6H4) (2-F) with a binding constant in MeOH exceeding that of 1-Mes2B-4-MePh2P-(C6H4) ([1]+) by at least 4 orders of magnitude. Structural and computational results indicate that the high fluorophilicity of [2]+ arises from both Coulombic and cooperative effects which lead to formation of a B-F→P interaction with a F→P distance of 2.666(2) A. These results, which are supported by NBO and AIM analyses, show that the latent phosphorus-centered Lewis acidity of the phosphonium moiety in [2]+ can be exploited to enhance fluoride binding via chelation. Copyright
